Dimethylformamide → Mofegiline

HRID 376096Notes

Reaction equation

HRID 376096 reaction equation
C([N-:3][CH:4]=O)=O.[Na+].C(#N)C.CN(C)C=O.ClC/[C:17](=[CH:27]/[F:28])/[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1>O>[NH2:3][CH2:4]/[C:17](=[CH:27]/[F:28])/[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6342AcetonitrileHCID 9815806(E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butaneHCID 10877056Sodium Diformylamide

Product 1

HCID 6437850Mofegiline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine sodium diformylamide (28.8 g, 0.31 mol), acetonitrile (360 g), and N,N-dimethylformamide (48 g). Add (E)-1-chloro-2-(fluoromethylene)-4-(p-fluorophenyl)butane (50.6 g, 0.23 mol). Heat to reflux. After 5 hours, cool to ambient temperature. Add water (466 g) and stir for 15 minutes. After 30 minutes, the aqueous layer is removed. Evaporate the organic layer in vacuo to give the title compound. 1H NMR (CDCl3, 300 MHz) δ2.28 (m, 2H), 2.72 (m, 2H), 4.07 (d , J=3Hz, 2H), 6.74 (d, J=81Hz, 1H), 6.94 (m, 2H), 7.13 (m, 2H), 8.73 (s, 2H).

Workup

  1. temperatureHeat to reflux
  2. waitAfter 30 minutes
  3. customthe aqueous layer is removed
  4. customEvaporate the organic layer in vacuo

Sources & evidence

ORD record
ord-850b8048dd1247e5be6b8ae2bcd7c948
Source dataset
uspto-grants-1996_01
Patent number
US05488188

Reaction notes

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